A Date With Death
by Freakinapplepiebaby
Summary: AU AIS Oneshot. It's one thing to help complete strangers move on to the after life. But what happens when the people Dean has to kill are the ones he loves? Warning: Character Death


_**So this is an AU to AIS. My friend and I came up with this being a possible plot before the show premiered and ever since I haven't managed to get out of my head. I however, am thankful the writers were nice and chose not to go in this direction. Anyways, now that my muse is back and working over time, I thought I'd post this and give you guys a break from "Of Coffee Shops". Anyways, I hope you enjoy!**_

If Dean had known what was going to happen today, and what a truly sick sense of humor Death had, he would have never had made the bet. And now as he knelt in the rubble of his life; flames and glass and metal strewn around a cement construction site, he wished more than ever that he could go back in time and never seek out Dr. Robert and never open this earth shattering can of worms. He heard her long before he felt her cold, comforting touch on his shoulder.

"Dean," Tessa breathed softly, trying her morbid tactic of comforting the bereaved.

"Are they safe then?" He asked through his sobs, his fingers digging deeper into the soft hair of the two bodies he cradled in his lap.

"Yes," Tessa said gently, "Your job is done. You saved them."

Dean let out a pained laugh, "Tessa, not trying to be rude or anything but do you think you could just not try and 'comfort' me anymore? I'm not sure I can take anymore."

Silence reined for a few more moments as Dean sobbed into the broken shells that were once warm and full of light. In the distance he heard the sounds of ambulances racing to the scene. Dean choked on a sob at the irony; they were too late.

'Hey Tessa?" Dean asked as the lights began to reflect on the shattered glass he was sitting in. Dean clutched harder to the two corpses; he knew that soon they would be dragged away from him as soon as the paramedics arrived; perks of being an invisible embodiment of the ultimate fear.

"Yes Dean?" She asked watching as the lights got closer. They had to leave; there were still so many souls to reap. She wanted to pry him away and force him to focus on his job, but she knew that it would be futile. Dean Winchester was the most stubborn soul she had ever met and he would do things in his own time.

"If…If I had waited." He started, his mind screaming in panic as the sirens tore through his thoughts. "If I had waited to, you know…could they have saved them?"

"No Dean." Tessa said firmly. "There was nothing they could have done for them. It was their time to go. All waiting would have done was to prolong their suffering."

"Ok,' Dean said brokenly.

The ambulance pulled up next to them and a team of paramedics rushed out and headed straight for the bodies lying together near the wreckage; where they had landed when they were thrown from the car. Tessa pulled Dean back just as the paramedics reached them and began to check for a pulse. When none was found they quickly brought blankets over and draped them over the forms until they could get them onto stretchers. Dean cried out as the blankets covered their bruised and bloodied faces. He tried to reach out for the blanket to rip it off, but it was like grabbing at water; impossible.

Tessa put a hand on his shoulder, "C'mon Dean. We still have work to do."

Dean shrugged her off. He couldn't do this. He'd already lost so much and for what? A soul his brother didn't even want back; a soul that every demon and angle they'd come upon said would kill his little brother if he got it back. It was all for not. What a waste, what a stupid waste…

**10 Minuets Earlier…**

Thus far the bet had been easy. Dean couldn't see what all the fuss was about. A day being Death? Piece of cake. Dean figured Death should just go retrieve Sam's soul now, because he had this wager in the bag. A robber, a heart attack, and an addict later and this job seemed like a walk in the park. Please, he'd killed monsters that were tougher on his conscience than these guys. After all, it isn't like he knew them; all it took was a touch.

So why did he feel the cold clammy hands of dread wrap around his throat all of a sudden? Dean knew this road; he drove it enough times when they first moved to Battle Creek to not. Hell, he even recognized the park he could see on the right. He and Ben had gone there once or twice to throw a ball around in between hunts. He wasn't frighten about the fact that he was standing in the middle of Capital Ave. nor Bailey Park; no, what had him scared shitless was the fact that he recognized the car, or the tangled remains of the 2000 Chevy Trailblazer wrapped around a median. Dean swallowed hard and looked to Tessa for reassurance.

"They were thrown from the car when a trucker cut them off and the driver swerved to avoid getting side swiped and they rolled." Tessa explains gently.

Dean sees them now, two small bodies lying a few feet from the smashed end the car. He can tell from the way they are contorted that they are in a lot of pain and probably past help.

'_Of course their past help!'_ Dean though angrily, _'that's why Death is here.'_

Dean prays urgently as he approaches the frames that he won't see what he fears he will. They lay next to each other; a woman and a child, their bodies broken beyond repair. Dean lets out a distressed yell as he spies a black curl hanging away from blood matted hair. His worst fears are confirmed.

"You can't be serious," he shouts to Tessa, turning his head away from the horrible sight. "This is some kinda of joke, or a dream right? You can't seriously expect me to do this?"

"Dean," Tessa says, "I need to take them. You have to do this. Look at how much pain they're in. You know that there's nothing that can be done to save them…except for you Dean. You can save them from their suffering."

Dean's a sobbing mess as he lets out a yell and drops to his knees threading his fingers gently in brunette hair. "No…" he chokes.

"Please, you have to let me reap them." Tessa sooths kneeling down next to them and stroking the little boys head. He gasps in pain.

"Get away from them!" He screams at her catching her wrist and wrenching it away. "Don't you touch him!"

Dean wants to take the boy's hand, wants to wrap him in comfort and love; but he knows his touch will do nothing but end his too short of a life.

"Ben!" He sobs grabbing his arms in an attempt to prevent himself from accidentally touching them. "Lisa….I…why?" He throws the last part at Tessa.

"Because it's their time Dean," she says firmly. "You know better than anyone that death can't be cheated."

"No…I can't let this happen!" He yells fisting his hair and doubling over in grief.

"Dean," Tessa says softly placing a gently hand on his shoulder. "It's already happened. All you can do now is let them go. Free them from the pain they are in right now, please."

Lisa lets out a pained cough that sends blood across her lips. "I can't. I won't even get a chance to say goodbye! To tell them how much I love them!"

"Dean, they are just like every soul that has ever walked this earth. Every single one gets a chance to see Death; they are no different."

"But I thought…" Dean choked.

"You thought what? That you have to be cold and calm. That you can't give real words of comfort. Dean, it's our job to help souls find the light. To push them in the right direction. You tell souls what they need to hear to move on; that's your job."

They both were ripped from their conversation with a scream of agony; Lisa had started to come to.

"Ben…Ben?" She croaked as she tried to force herself to look for her son.

Dean watched in horror as she struggled to move, the pain written clearly on her face.

"Do it now Dean. You have to do it." Tessa whispered in his ear, squeezing his shoulder comfortingly before she let go. Dean let out a wounded cry but he understood that he couldn't delay anymore. Dean knelt down besides Lisa and taking her head into his hands he kissed her as gently as he could. He felt her soul leave her body as her lips started to grow cold under his. When he looked up, he saw her and her look of utter confusion.

"Dean?" She asks timidly, she was scared. "Where am I? What's…Is that me?"

"Hi Lis," he chokes out brokenly, going to her in a swift motion and holding her as close to him as their physical spirits would allow. "I'm so sorry. I'm so sorry."

"Dean?" She tried to ask but they were both cut off by a cry of pain from Ben.

"Him too Dean," Tessa said softly, pulling Lisa away from Dean so he could bring home Ben.

Dean knelt down again and pulled the child he considered his son into his arms and wrapping his comforting arms around him kissed him gently on the forehead; like he used to when he tucked him in at night. He just held him softly as sobs began to rack his body again.

"Dean," came a young voice from behind him. Dean closed his eyes trying to gather the strength to turn around and see them both for the last time. He lowered Ben's body down and standing pulled Ben into his arms and sobbed into his hair. He then did the same to Lisa pulling her into a passionate, heart breaking kiss. They all held each other for a moment, finally realizing that this was it; the last they would see of each other.

"Dean," Tessa said intrusively. "It's time for them to go."

Dean nodded and pulled away. He tried to stop the tears from flowing, worried their blur would ruin this last sight of them.

"Where are we going?" Asked Ben softly. "I'm not sure I want to go."

Dean sighed and knelt down besides Ben and grabbed his face gently in his hands. "Yes you do buddy. It's beautiful there and there's nothing for you to do all day but have fun. It's warm and happy and everyone you love will be there for you, and they will never leave or grow old and they will never die."

"Are you coming with us?" Ben asked seriously. Dean felt a sob attempt to escape and he bit it back tersely, he had to keep it together, for their sakes.

"Not yet, Ben. But I'll be there sooner than you think." Dean wiped at his eyes trying in vain to stay strong. "Hey Buddy, can you do me a favor?"

"What Dean?" Ben asked with puzzlement. He couldn't understand why Dean was crying; didn't he say he was going someplace awesome?

"Can you be the man of the house and look after your mom for me until I get there?"

"Duh!" Ben said, "Dude, I was doing that before you showed up and long after you left…I will. You won't leave me in charge for too long right?"

Dean laughed bitterly, "I wouldn't dream of it kiddo." He pulled Ben tight again and tried to memorize every second of this moment. "I love you Ben, I want you to know that. I love you so much!"

"I love you too Dean." Ben whispered kissing his cheek. He then pulled away and Lisa was replacing his warmth.

"Thank you for everything," She said softly, her own tears mixing with his and bleeding into his flannel.

"I'm so sorry," Dean cried.

"Shhh," Lisa soothed, "Don't be! The moments I shared with you were the best ones of my life. I'm the one who should be sorry. I shouldn't have pushed you away. I was scared Dean that I was going to lose you again…I'm so sorry."

Dean pulled her back and kissed her for all he was worth. He felt a light start at the pit of his stomach and radiate outward, it felt like peace.

"I would've married you Lisa," he whispered softly. "You and Ben were the only things I've ever wanted so much in my life it hurt! I love you. I love you more than you will ever know."

"I know Dean," She kissed him one more last time. "I love you, I always will."

Tessa then stepped forward and gently grabbed Lisa's arm signaling that it was time. She stepped away and taking Ben's hand turned to Tessa.

"We're ready," She said resolutely. Tessa then wrapped her arms around them and in a flash of blinding white light all three of them were gone. Dean let out a cry of pure anguish and collapsed onto the road. He crawled his way over to their empty vessels and held them both in his arms. If Dean had known what was going to happen today, and what a truly sick sense of humor Death had, he would have never had made the bet. And now as he knelt in the rubble of his life; flames and glass and metal strewn around a cement construction site, he wished more than ever that he could go back in time and never seek out Dr. Robert and never open this earth shattering can of worms. He heard her, long before he felt her cold, comforting touch on his shoulder.

"Dean," Tessa breathed softly, trying her morbid tactic of comforting the bereaved.

"Are they safe then?" He asked through his sobs, his fingers digging deeper into the soft hair of the two bodies he cradled in his lap.

"Yes," Tessa said gently, "Your job is done. You saved them."

Dean let out a pained laugh, "Tessa, not trying to be rude or anything but do you think you could just not try and 'comfort' me anymore? I'm not sure I can take anymore."

**Now…**

Dean watched as the ambulance pulled away. He felt sick to his stomach. This whole exercise was a waste of time; even if Sam got his soul back, his sanity was only a temporary thing at best. Had Dean realized the price…He laughed as he thought of the irony as a situation. The only good thing to come of his day as Death was to comfort Ben and Lisa in the final moments of this world…

"Dean," Tessa said gently. "We have to keep moving."

Dean nodded and brushed his tears away.

'_What the hell,'_ he though, _'Might as well throw all my eggs in one basket._' The Winchester men were survivors; followed by death and by grief, their only choice was to keep moving on or lie down and hope to die. And as much as Dean would like nothing better than to take the ring off and lie in the middle of this Michigan road and wait for a car to put an end to him, he knew he couldn't do it. Dean had paid the ultimate price for Sam's soul and he'd be damned if Death cheated him out of that too.

Dean turned to Tessa and took her hand, "We've got work to do."

_**A/N: So it's a proven fact I can't write happy stuff. Anyways, I would love to hear feedback on this oneshot. Thanks so much for reading.**_


End file.
